TIWF: Coboating in the Caribbean

I’m proof that Instagram ads work because an intriguing Instagram ad got my attention and a few months later we ended up on a 65″ Catamaran in the Caribbean.

The ad sounded almost too good to be true… a “pay what you want*” boating trip with high-speed internet! A true digital nomad’s paradise. Reading online blogs it seems they had tried this once before and there had been some unexpected repairs that needed to be done to the boat and they had to abandon the project for cost reasons. This year they said they were partnering with an existing similar boat project and captain that had plans to be in the Caribbean.

Despite the sense of too good to be true, Helena and I decided to apply, were accepted, and pay the $300 “down payment to the kitty”. In the weeks leading up to it, I kept checking social media to try and determine if this was really legit. They were a few Instagram posts and stories that made me feel like it was indeed going, but about 2 weeks before we were supposed to go there was a bad Facebook review that gave us a bit of a pause. This person said that the organizer was a bit coercive when it came to the “pay what you want” policy and got angry when she wanted to pay less than he expected. So that part *was* too good to be true and that actually made me a feel a bit better. I messaged that reviewer and she said that the trip itself was actually really great, apart from the payment confusion. As a result, I contacted the organizer, Karsten, before we were scheduled to leave and asked him what he thought was a fair amount. I’m not going to disclose what he said, but I thought it sounded more than fair for what we were getting and so I was thankful to have that out of the way.

We were told the boat would be around Martinique and I confirmed with Karsten a couple of days before that they were still planning on being in Martinique so we wouldn’t have to arrange a transfer to another island. The day of I was able to see the exact harbor that they were on the map and confirm with Karsten that we just had to get ourselves to Sainte Anne, which was about 40km from the airport. If our flight hadn’t been delayed by about 3 hours due to maintenance we would have likely been able to take a fairly inexpensive “Taxi Collectiv”, which is the bus service around the island. But unfortunately they don’t run after 6pm and so we had to hail a taxi, which ended up being pretty pricey. I messaged Karsten on Whatsapp when we arrived at the bay and he and another fellow crew member pulled up at the dock with the dinghy in just a few minutes.

As we sped towards the boat in the harbor on the dinghy I was struck with a bit of surreality that I’m actually doing this. I’m actually going to spend the next 7 days on a boat with a half dozen strangers. As we arrived on the boat and said hello to everyone what struck me was what an international group of people was on the boat. We were actually the only Americans! But being from Miami, that wasn’t a particularly strange experience. Everyone spoke English as well and so it was the universal language. Three of the crew members, including Karsten, the organizer, and Martin the boat owner/captain were German so there was a lot German spoken as well.

Karsten and another crew member showed us to our room and I was immediately struck by how fancy and new the boat was. We had a queen bed, a private bathroom, and a TV (but we never even turned it on!) in our cabin. The only thing was I kind of started to panic a little bit when I realized the boat only had German power sockets (type f) and I hadn’t brought an international power adapter. I think my brain assumed that since we were still in the general US hemisphere that of course, the boat would have would be US power plugs. But that was a total failure on my part because Martinique doesn’t even use the US power plugs and I knew the boat had been sailed over from across the Atlantic. So my stupid American-centredness bit me.

Luckily as I would soon learn, there were ample adapters and fellow MacBook Pro USB-C power adapters that everyone shared on deck so computer power wasn’t really ever a true problem. USB-C and MagSafe adapters were the most universal form of power onboard.

The next day I woke up pretty early due to the fact that the sun comes up very early in Martinique because it’s quite east of the US, but it was actually the same time zone in Miami as it was in Martinique. I woke up and aimlessly kind of explored around the boat as a few people made their way up on deck as well and we had some small talk. Luckily someone made coffee at some point as I didn’t have the foggiest clue how to. After a few hours and the captain did a bit of customs paperwork on shore we embarked on our first sailing journey.

The ocean was pretty calm as we were anchored in the bay, but as we got out to the open ocean and set sail the waves definitely picked up. I’ve been seasick before on diving boats, mostly because diving boats tend to be small single hull boats and aren’t particularly stable so I was curious how I’d do on a bigger, dual hull boat. For about the first hour I was fine, but then I went to check on Helena who was still asleep below deck, and when I came back I was not fine… I immediately felt my stomach and bowels’ desire to evacuate. I tried staring at the horizon which is what I was told on dive boats, but it wasn’t really working. I felt the sweat pouring down my face as I tried to keep it in. And then one of the other crew members looked at me and noticed I looked really pale. They told me to lay down and close my eyes. Initially, I protested, but as soon as I did I started to feel better. Eventually, I got my headphones and enjoyed a couple of podcasts for the next hour or two as we crossed from Martinique to St Lucia.

We sailed into the first bay on the west side of St Lucia, Rodney Bay and had a bit of déjà vu. I realized I had been to this exact bay a few years earlier and stayed at the Sandals Grande St. Lucian there. The first time I had arrived by helicopter because it’s about a 3 hour car ride through windy mountainous roads. Now I was arriving by boat!

This bay seemed strangely quiet. Almost deserted. It seemed like most of the life was restricted to the hotel and resort beaches, but in the general harbor area that wasn’t really that much life. There was a “water park” slightly offshore of one of the hotels that a couple of the crew decided to swim to. Turns out that the staff saw them and said they had to pay $15 to use the park and so they decided it wasn’t worth it.

I went with the captain ashore to do customs because I was curious about how that worked on a boat. I was surprised to learn that you have to do immigration and customs even sailing a few hours between islands because Martinique was a French territory and St Lucia is a British territory. And apparently Karsten said the last time they checked in there it was free, but we found out that because it was the weekend they charge a $40 fee. Guess something I’ll have to remember next time I’m sailing around St Lucia! Because there wasn’t much shore life we decided to stay on the boat for the night and cook food and play games.

The next day we chilled in the bay for the morning and did a SCUBA lesson for one of the crew who wasn’t certified before embarking to the next bay and my favorite location: Marigot Bay. It was a very small and narrow bay, but it was flanked by palm trees and mangroves on all sides so you really felt like you were in the jungle. There was the most amazing Indian restaurant there called Masala Bay that we booked a reservation at and that night we were basically the only people dining. The service and food were impeccable. We also went to a great little bar on the other side of the bay called Doolittle’s (named after Dr. Doolittle because they filmed a scene there) that had pool tables and very strong, but inexpensive drinks. At sunset, we witnessed one of the most spectacular sunsets I’ve ever seen. So beautiful that everyone was crowding around with their phones and cameras to capture the moment.

The next day we set sail and went in search of a good diving location because St Lucia is known for its spectacular coral reefs, as I’ve witnessed the last time I was diving in St. Lucia. We ended up finding a mooring just on the edge of the protected marine park. Not knowing exactly what the rules or fees were for diving we asked a local boat that stopped by and was selling handmade necklaces and he said there were no fees. So Karsten, Mattius, and I suited up and dove in. We initially had a bit of trouble finding the reef, but we saw another dive group and went their direction. And that’s when we saw some truly amazing reefs that were plentiful with wildlife. At one point I even saw a turtle, which is always the magical unicorn creature I’m looking for on dives, but rarely see.

On our swim back to the boat, a dive boat drove up to us and informed us that our other boat friend was incorrect and that there’s a permit process for diving in St. Lucia and you have to dive with a St. Lucia divemaster. They even said violating that was a $5,000 fine. Later that day when a Marine reserve ranger came up to our boat and was talking with the captain I was pretty scared that we were going to be subject to that fine. But there were surprisingly chill and the marine ranger was a divemaster himself so we were able to arrange to pay for the mooring fees and schedule a dive with him the next morning.

After an awesome dive the next morning, we kept on sailing further south to Soufriere where we were escorted into the bay by a local that our captains had made friends with last time they were there. He was really helpful and ferried us to and from the shore and arranged for transportation and a tour of some nature hikes inland. Later in the evening, we went ashore and visited some of the local restaurants and bars. The town was very isolated from the rest of the island and so it wasn’t very touristy. That also meant that the food and drinks were extremely cheap! 5EC (East Carribean) for a beer was less than $2 USD. Living in Miami, I haven’t even had a beer for less than $5 USD! I loved how Martin and Karsten really cared about the locals and we were able to hang out with them. In the past when I’ve been in the Carribean on a resort you feel very isolated from the people that actually live there.

The next day most of the crew went on the nature hike. I had to stay behind because there was a website launch that was supposed to be 2 weeks before but was unfortunately delayed to be during the trip. Part of the concept of Coboat is that it’s supposed to kind of be a coworking experience combined with boating. So you wouldn’t think its quite possible, but the boat had Wifi. I believe the connection was through 2 cellular connections merged together for a bit more bandwidth. As we were sailing around the shore for the majority of the time we almost always had a signal and the speed was decent. A couple of times the internet connection ran out of paid bandwidth and it would have to be refilled, but I usually took that time to take a break from working or I could just tether to my phone and use Verizon’s daily 500MB allowance they gave me. A couple of times I realized how fast 500MB can go with an LTE connection.

Of the crew, I think I was the only one with an active business that I had to work fairly consistently on most days. But Helena had a couple of commissions so she was also fairly busy. And a pair of brothers onboard were also working on a new app together that they stayed up late into the night most nights to work on.

For me, I wish I had been a little less busy so I could have done things like going ashore for the nature hike or staying up a bit later hanging out, but overall I really loved the merger of work and recreation. To be able to get in the morning, get a few hours of work done, and then dive in the water straight from the boat and spend an hour with the fishes was paradise.

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